HK1070359A1 - Benzimidazole derivatives and their use as gnrh antagonists - Google Patents

Benzimidazole derivatives and their use as gnrh antagonists

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Publication number
HK1070359A1
HK1070359A1 HK05103022A HK05103022A HK1070359A1 HK 1070359 A1 HK1070359 A1 HK 1070359A1 HK 05103022 A HK05103022 A HK 05103022A HK 05103022 A HK05103022 A HK 05103022A HK 1070359 A1 HK1070359 A1 HK 1070359A1
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Hong Kong
Prior art keywords
halo
nht
heterocycloalkyl
aryl
heteroaryl
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HK05103022A
Inventor
Poitout Lydie
Brault Valerie
Ferrandis Eric
Thurieau Christophe
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Scras
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Application filed by Scras filed Critical Scras
Publication of HK1070359A1 publication Critical patent/HK1070359A1/en

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    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • A61P13/00—Drugs for disorders of the urinary system
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    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
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    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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    • C07D471/10—Spiro-condensed systems

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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

2-(Alkylamino or alkylthio)-5-(aminocarbonyl or aminomethyl)-benzimidazole derivatives (I) are new. 2-(Alkylamino or alkylthio)-5-(aminocarbonyl or aminomethyl)-benzimidazole derivatives of formula (I), in racemic or enantiomer form or any combination of these forms, and their salts are new. A = CH2 or CO; Y = S or NH; R1, R2 = H, 1-8C alkyl, 5-9C bicycloalkyl (optionally substituted (os) by one or more T) or -(CH2)a-X; or NR1R2 = heterocycloalkyl, heterobicycloalkyl or a spiro or fused piperidine group of formula (i), (ii), (iii) or (iv) (all os by one or more of -(CH2)c-X''-Y'', oxo, hydroxy, halo, nitro or cyano); T = 1-6C alkyl; X = NH2, NHT, NT2, adamantyl, arylcarbonyl, 1,4-benzodioxanyl, 1,3-benzodioxolyl, indanyl or tetralinyl or 3-7C cycloalkyl, heterocycloalkyl, aryl or heteroaryl (os by one or more of -(CH2)b-X'-Y', halo, oxo, NO2, CN, NH2, NHT, NT2, OH or N3); X' = O, S, C(O), C(O)O, NHC(O), NHSO2 or direct bond; Y' = T (os by one or more halo) or heteroaryl, aryl or heterocycloalkyl (all os by one or more of T, OT, halo, NO2, CN, NH2, CF3, OCF3, OH, N3, NHT or NT2); X'' = O, C(O), C(O)O or direct bond; Y'' = T, NH2, NHT, NT2, 3-7C cycloalkyl, heterocycloalkyl or aralkyl; aryl or heteroaryl (both os by one or more of T, OT, COT, halo, OH, NO2, CN, CF3, OCF3, NH2, NHT or NT2); or 1,4-benzodioxanyl, 1,3-benzodioxolyl or benzimidazol-2-on-1-yl; a = 0-6; b = 0-2; c = 0-4; R3 = -(CH2)c-W3-(CH)2d-Z3; W3 = direct bond, CH(OH) or C(O); Z3 = T, adamantyl, aryl, heteroaryl, 1,4-benzodioxanyl, 1,3-benzodioxolyl or anthraquinonyl (where all aryl groups are os by one or more of -(CH2)e-V3-Y3, halo, NO2, CN, N3 or OH; V3 = O, S, C(O), C(O)O, SO2 or direct bond; Y3 = T, os by one or more halo, NH2, NHT, NT2, CH2COPh, heterocycloalkyl or aryl; c, d, e = 0-4; R4 = -(CH2)f-R''4; R''4 = heterocycloalkyl containing at least one N (os by T or aralkyl); heteroaryl containing at least one N (os by T); or -NW4W'4; W4 = H, T or cycloalkyl; W'4 = -(CH2)g-Q4-Z4; Q4 = -CH2CH(OH)-(CH2)h-(O)i-(CH2)j or -C(O)O; Z4 = H, 1-8C alkyl (os by one or more of OT, ST, SST and OH), 2-6C alkenyl, 2-6C alkynyl, 3-7C cycloalkyl (os by one or more alkyl, COOT or -T-OH), cyclohexenyl, adamantyl, heteroaryl, aryl (os by one or more of -(CH2)k-V4-Y4, OH, NO2, halo or CN), 1,4-benzodioxanyl or 1,3-benzodioxolyl; V4 = O, S, NHC(O) or direct bond; Y4 = T (os by NT2 or one or more halo), NH2, NHT, NT2, aralkyl or heterocycloalkyl; f, g = 0-4; h, i, j = 0 or 1; and k = 0-4.
HK05103022A 2001-12-21 2005-04-11 Benzimidazole derivatives and their use as gnrh antagonists HK1070359A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0116647A FR2833948B1 (en) 2001-12-21 2001-12-21 NOVEL BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS MEDICAMENTS
PCT/FR2002/004477 WO2003053939A1 (en) 2001-12-21 2002-12-20 Benzimidazole derivatives and their use as gnrh antagonists

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HK1070359A1 true HK1070359A1 (en) 2005-06-17

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US (2) US7495110B2 (en)
EP (1) EP1467974B1 (en)
JP (1) JP4418679B2 (en)
KR (1) KR100927500B1 (en)
CN (1) CN100334077C (en)
AT (1) ATE370126T1 (en)
AU (1) AU2002365016B2 (en)
CA (1) CA2471044C (en)
CZ (1) CZ2004819A3 (en)
DE (1) DE60221901T2 (en)
ES (1) ES2291544T3 (en)
FR (1) FR2833948B1 (en)
HK (1) HK1070359A1 (en)
HU (1) HU228339B1 (en)
NO (1) NO327105B1 (en)
NZ (1) NZ533558A (en)
PL (1) PL212986B1 (en)
RU (1) RU2294326C2 (en)
WO (1) WO2003053939A1 (en)

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